Selective oxidation of phenol and anisole derivatives to quinones with hydrogen peroxide and polymer-supported methylrhenium trioxide systems

Tetrahedron

Volumn 58, Issue 42, 2002, Pages 8493-8500

  Saladino, Raffaele ^a   Neri, Veronica ^a   Mincione, Enrico ^a   Filippone, Paolino ^b  

^a UNIVERSITY OF TUSCIA   (Italy)

^b UNIVERSITY OF URBINO   (Italy)

Author keywords

Catalysis; Natural products; Oxidation; Phenols

Indexed keywords

2 METHOXY 4 (1' ETHANYL 2' OLO) 1,4 BENZOQUINONE; 2 METHOXY 5 METHYL 1,4 BENZOQUINONE; 2 TERT BUTYL 5 PENTADECYL 1,4 BENZOQUINONE; 2,3,5 TRIMETHYLBENZOQUINONE; 2,6 DIMETHYLBENZOQUINONE; 4 ETHYL 1,2 BENZOQUINONE; 4 PENTADECYL 1,2 BENZOQUINONE; ALCOHOL DERIVATIVE; ANISOLE DERIVATIVE; BENZOQUINONE DERIVATIVE; HYDROGEN PEROXIDE; METHYLBENZOQUINONE; OXYGEN; PHENOL DERIVATIVE; POLYMER; RHENIUM COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; ATOM; CATALYSIS; CATALYST; COST EFFECTIVENESS ANALYSIS; DRUG SYNTHESIS; HYDROGEN BOND; MOLECULAR INTERACTION; MOLECULAR RECOGNITION; OXIDATION; PRIORITY JOURNAL;

EID: 0037078245     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)01025-6     Document Type: Article

References (78)

1. (a) Nishina A., Uchibori T. Agric. Biol. Chem. 55:1991;2395-2398.
2. (b) Letcher R.M., Wong M.C. J. Chem. Soc., Perkin Trans. 1. 1992;3035-3037 Rodriguez J., Quiñoà F., Riguera R., Peters B.M., Abrell L.M., Crews P. Tetrahedron. 48:1992;6667-6680.
3. (b) Letcher R.M., Wong M.C. J. Chem. Soc., Perkin Trans. 1. 1992;3035-3037 Rodriguez J., Quiñoà F., Riguera R., Peters B.M., Abrell L.M., Crews P. Tetrahedron. 48:1992;6667-6680.
4. (c) Hakura A., Mochida H., Tsutsur Y., Yamatsu K. Mutat. Res. 347:1994;37-43.
5. (d) Liu M., Koya S., Furuta H., Matsuzaki S. J. Med. Sci. 23:1996;85-93.
6. (e) Peter R. Pestic. Sci. 47:1996;287-296.
7. (f) Floreani M., Forlin A., Bellin S., Carpanedo F. Gen. Pharmacol. 27:1996;873-878 Schulte T.W., Neckers L.M. Cancer Chemother. Pharmacol. 42:1998;273-279 Lund A.K., Adsernen A., Nyman U. Phytomedicine. 5:1998;199-203 Geiselhart L.A., Christian T., Minnear F., Freed B.M. Toxicol. Appl. Pharmacol. 143:1997;30-36.
8. (f) Floreani M., Forlin A., Bellin S., Carpanedo F. Gen. Pharmacol. 27:1996;873-878 Schulte T.W., Neckers L.M. Cancer Chemother. Pharmacol. 42:1998;273-279 Lund A.K., Adsernen A., Nyman U. Phytomedicine. 5:1998;199-203 Geiselhart L.A., Christian T., Minnear F., Freed B.M. Toxicol. Appl. Pharmacol. 143:1997;30-36.
9. (f) Floreani M., Forlin A., Bellin S., Carpanedo F. Gen. Pharmacol. 27:1996;873-878 Schulte T.W., Neckers L.M. Cancer Chemother. Pharmacol. 42:1998;273-279 Lund A.K., Adsernen A., Nyman U. Phytomedicine. 5:1998;199-203 Geiselhart L.A., Christian T., Minnear F., Freed B.M. Toxicol. Appl. Pharmacol. 143:1997;30-36.
10. (f) Floreani M., Forlin A., Bellin S., Carpanedo F. Gen. Pharmacol. 27:1996;873-878 Schulte T.W., Neckers L.M. Cancer Chemother. Pharmacol. 42:1998;273-279 Lund A.K., Adsernen A., Nyman U. Phytomedicine. 5:1998;199-203 Geiselhart L.A., Christian T., Minnear F., Freed B.M. Toxicol. Appl. Pharmacol. 143:1997;30-36.
11. (g) Mossa S.J., Muhammad I., Ramadan A.F., Mirza H.H., El-Feraly S.F., Hufford D.C. Phytochemistry. 50:1999;1063-1068.
12. (h) Deml R., Huth A. Naturwissenschatten. 87:2000;80-82.
13. (i) Miles D.H., Payne M. Tetrahedron. 57:2001;5769-5772.
14. (j) Gutenter A., Ioset J.R., Queiroz E.F., Foggin C.M., Hostettmann K. Phytochemistry. 58:2001;631-635.
15. Quideau S., Pouysegu L. OPPI Org. Prep. Proced. Int. 31:1999;617-668. and references circo therein.
16. (a) Cherkaoni O., Nebois P., Fillion H., Domard M., Fenet B. Tetrahedron. 52:1996;9499.
17. (b) Itoh S., Ogino M., Haranou S., Terasaka T., Ando T., Komatsu M., Ohshiro Y., Fukuzumi S., Kano K., Takagi K., Ideka T. J. Am. Chem. Soc. 117:1995;1485.
18. Takeya T., Moregi S., Itoh T., Tobinaga S. Chem. Pharm. Bull. 45:1997;613.
19. Brimble M.A., Duncalf L.J., Phythiom S.J. J. Chem. Soc., Perkin Trans. 1. 1997;1399.
20. Feldman K.S., Quideau S., Appel H.M. J. Org. Chem. 61:1996;6656.
21. (a) Vanderlei J.M.L., Coelho F., Almeida W.P. Tetrahedron: Asymmetry. 8:1997;2781.
22. (b) Almeida W.P., Corriera C.R. Tetrahedron Lett. 35:1994;1367.
23. (a) Kinugawa M., Masuda Y., Arai H., Nishikawa H., Osaga T., Tomiok S., Kasai M. Synthesis. 1996;633.
24. (b) Kato N., Sugaya T., Mimura T., Ikuta M., Kato S., Kuge Y., Tomioka S., Kasai M. Synthesis. 1997;625.
25. Boyd V.A., Sulikowski G.A. J. Am. Chem. Soc. 117:1995;8472.
26. Brumble M.A., Phythian S.J. Tetrahedron Lett. 34:1993;5813.
27. Tamura Y., Sasho M., Akar S., Wada A., Kita Y., Tetrahedron. 40. 1984;4539.
28. Moser W., Howie R.A. Inorg. Phys. Theor. J. Chem. Soc. A. 1968;3039.
29. Shishido K., Goto K., Meyoshi S., Takaishi T., Shibuya M. J. Org. Chem. 59:1994;406.
30. Watanabe M., Shinoda E., Shimizu Y., Furukawa S., Iwao M., Kuraishi T. Tetrahedron. 43:1987;5281.
31. Kozhevnikov I.V. Chem. Rev. 98:1998;171-198.
32. Murahashi S.I., Naota T., Miyaguschi N., Noda S. J. Am. Chem. Soc. 118:1996;2509.
33. (a) Artaud I., Aziza K.B., Chopard C., Mansuy D. J. Chem. Soc., Chem. Commun. 1991;31-33.
34. (b) Artaud I., Aziza K.B., Mansuy D. J. Org. Chem. 58:1993;3373-3380.
35. (c) Murtinho D., Pineiro M., Pereira M.M., Rocha G., Antonio M.A., Arnaut L.G., da Graga M.M., Burrows H.D. J. Chem. Soc., Perkin Trans. 2. 2000;2441-2447.
36. Krohn K. Synthesis. 1997;1115.
37. Suresh S., Skaria S., Ponrathnam S. Synth. Commun. 26:1996;2113.
38. Hashemi M.M., Beni Y.A. J. Chem. Res. (S). 1998;138.
39. Sakamoto T., Yonehara H., Pac C. J. Org. Chem. 62:1997;3194.
40. Ramani A., Suresh S., Sasidharan M., Sudalai A., Chanda B.M. J. Chem. Res. (S). 1996;474-475.
41. Beattie I.R., Jones P.J. Inorg. Chem. 18:1979;2318.
42. (a) Herrmann W.A., Fischer R.W., Marz D.W. Chem. Rev. 97:1997;3197-3246.
43. See, for example, (b) Herrmann W.A., Fischer R.W., Marz D.W. Angew. Chem, Int. Ed. Engl. 30:1991;1638 (c) Al-Ajlouni A.M., Espenson J.H. J. Org. Chem. 61:1996;3969-3976 (d) Adam W., Mitchell C.M. Angew. Chem., Int. Ed. Engl. 35:1996;533-535 (e) Copéret C., Adolfsson H., Sharpless K.B. J. Chem. Soc., Chem. Commun. 1997;1915 (f) Herrmann W.A., Kratzer R.M., Ding H., Glas H., Thiel W.R. J. Organomet. Chem. 555:1998;293 (g) Adam W., Mitchell C.M., Saha-Moller C.R., Weichold O. J. Am. Chem. Soc. 121:1999;2097-2103 (h) Saladino R., Carlucci P., Danti M.C., Crestini C., Mincione E. Tetrahedron. 56:2000;10031-10037 (i) Bernini R., Mincione E., Cortese M., Aliotta G., Saladino R. Tetrahedron Lett. 42:2001;5401-5404 (j) Iskra J., Bonnet-Delpon D., Bégné J.P. Tetrahedron Lett. 43:2002;1001-1003 (k) Zhu Z., Espenson J.H. J. Org. Chem. 60:1995;7728.
44. See, for example, (b) Herrmann W.A., Fischer R.W., Marz D.W. Angew. Chem, Int. Ed. Engl. 30:1991;1638 (c) Al-Ajlouni A.M., Espenson J.H. J. Org. Chem. 61:1996;3969-3976 (d) Adam W., Mitchell C.M. Angew. Chem., Int. Ed. Engl. 35:1996;533-535 (e) Copéret C., Adolfsson H., Sharpless K.B. J. Chem. Soc., Chem. Commun. 1997;1915 (f) Herrmann W.A., Kratzer R.M., Ding H., Glas H., Thiel W.R. J. Organomet. Chem. 555:1998;293 (g) Adam W., Mitchell C.M., Saha-Moller C.R., Weichold O. J. Am. Chem. Soc. 121:1999;2097-2103 (h) Saladino R., Carlucci P., Danti M.C., Crestini C., Mincione E. Tetrahedron. 56:2000;10031-10037 (i) Bernini R., Mincione E., Cortese M., Aliotta G., Saladino R. Tetrahedron Lett. 42:2001;5401-5404 (j) Iskra J., Bonnet-Delpon D., Bégné J.P. Tetrahedron Lett. 43:2002;1001-1003 (k) Zhu Z., Espenson J.H. J. Org. Chem. 60:1995;7728.
45. See, for example, (b) Herrmann W.A., Fischer R.W., Marz D.W. Angew. Chem, Int. Ed. Engl. 30:1991;1638 (c) Al-Ajlouni A.M., Espenson J.H. J. Org. Chem. 61:1996;3969-3976 (d) Adam W., Mitchell C.M. Angew. Chem., Int. Ed. Engl. 35:1996;533-535 (e) Copéret C., Adolfsson H., Sharpless K.B. J. Chem. Soc., Chem. Commun. 1997;1915 (f) Herrmann W.A., Kratzer R.M., Ding H., Glas H., Thiel W.R. J. Organomet. Chem. 555:1998;293 (g) Adam W., Mitchell C.M., Saha-Moller C.R., Weichold O. J. Am. Chem. Soc. 121:1999;2097-2103 (h) Saladino R., Carlucci P., Danti M.C., Crestini C., Mincione E. Tetrahedron. 56:2000;10031-10037 (i) Bernini R., Mincione E., Cortese M., Aliotta G., Saladino R. Tetrahedron Lett. 42:2001;5401-5404 (j) Iskra J., Bonnet-Delpon D., Bégné J.P. Tetrahedron Lett. 43:2002;1001-1003 (k) Zhu Z., Espenson J.H. J. Org. Chem. 60:1995;7728.
46. See, for example, (b) Herrmann W.A., Fischer R.W., Marz D.W. Angew. Chem, Int. Ed. Engl. 30:1991;1638 (c) Al-Ajlouni A.M., Espenson J.H. J. Org. Chem. 61:1996;3969-3976 (d) Adam W., Mitchell C.M. Angew. Chem., Int. Ed. Engl. 35:1996;533-535 (e) Copéret C., Adolfsson H., Sharpless K.B. J. Chem. Soc., Chem. Commun. 1997;1915 (f) Herrmann W.A., Kratzer R.M., Ding H., Glas H., Thiel W.R. J. Organomet. Chem. 555:1998;293 (g) Adam W., Mitchell C.M., Saha-Moller C.R., Weichold O. J. Am. Chem. Soc. 121:1999;2097-2103 (h) Saladino R., Carlucci P., Danti M.C., Crestini C., Mincione E. Tetrahedron. 56:2000;10031-10037 (i) Bernini R., Mincione E., Cortese M., Aliotta G., Saladino R. Tetrahedron Lett. 42:2001;5401-5404 (j) Iskra J., Bonnet-Delpon D., Bégné J.P. Tetrahedron Lett. 43:2002;1001-1003 (k) Zhu Z., Espenson J.H. J. Org. Chem. 60:1995;7728.
47. See, for example, (b) Herrmann W.A., Fischer R.W., Marz D.W. Angew. Chem, Int. Ed. Engl. 30:1991;1638 (c) Al-Ajlouni A.M., Espenson J.H. J. Org. Chem. 61:1996;3969-3976 (d) Adam W., Mitchell C.M. Angew. Chem., Int. Ed. Engl. 35:1996;533-535 (e) Copéret C., Adolfsson H., Sharpless K.B. J. Chem. Soc., Chem. Commun. 1997;1915 (f) Herrmann W.A., Kratzer R.M., Ding H., Glas H., Thiel W.R. J. Organomet. Chem. 555:1998;293 (g) Adam W., Mitchell C.M., Saha-Moller C.R., Weichold O. J. Am. Chem. Soc. 121:1999;2097-2103 (h) Saladino R., Carlucci P., Danti M.C., Crestini C., Mincione E. Tetrahedron. 56:2000;10031-10037 (i) Bernini R., Mincione E., Cortese M., Aliotta G., Saladino R. Tetrahedron Lett. 42:2001;5401-5404 (j) Iskra J., Bonnet-Delpon D., Bégné J.P. Tetrahedron Lett. 43:2002;1001-1003 (k) Zhu Z., Espenson J.H. J. Org. Chem. 60:1995;7728.
48. See, for example, (b) Herrmann W.A., Fischer R.W., Marz D.W. Angew. Chem, Int. Ed. Engl. 30:1991;1638 (c) Al-Ajlouni A.M., Espenson J.H. J. Org. Chem. 61:1996;3969-3976 (d) Adam W., Mitchell C.M. Angew. Chem., Int. Ed. Engl. 35:1996;533-535 (e) Copéret C., Adolfsson H., Sharpless K.B. J. Chem. Soc., Chem. Commun. 1997;1915 (f) Herrmann W.A., Kratzer R.M., Ding H., Glas H., Thiel W.R. J. Organomet. Chem. 555:1998;293 (g) Adam W., Mitchell C.M., Saha-Moller C.R., Weichold O. J. Am. Chem. Soc. 121:1999;2097-2103 (h) Saladino R., Carlucci P., Danti M.C., Crestini C., Mincione E. Tetrahedron. 56:2000;10031-10037 (i) Bernini R., Mincione E., Cortese M., Aliotta G., Saladino R. Tetrahedron Lett. 42:2001;5401-5404 (j) Iskra J., Bonnet-Delpon D., Bégné J.P. Tetrahedron Lett. 43:2002;1001-1003 (k) Zhu Z., Espenson J.H. J. Org. Chem. 60:1995;7728.
49. See, for example, (b) Herrmann W.A., Fischer R.W., Marz D.W. Angew. Chem, Int. Ed. Engl. 30:1991;1638 (c) Al-Ajlouni A.M., Espenson J.H. J. Org. Chem. 61:1996;3969-3976 (d) Adam W., Mitchell C.M. Angew. Chem., Int. Ed. Engl. 35:1996;533-535 (e) Copéret C., Adolfsson H., Sharpless K.B. J. Chem. Soc., Chem. Commun. 1997;1915 (f) Herrmann W.A., Kratzer R.M., Ding H., Glas H., Thiel W.R. J. Organomet. Chem. 555:1998;293 (g) Adam W., Mitchell C.M., Saha-Moller C.R., Weichold O. J. Am. Chem. Soc. 121:1999;2097-2103 (h) Saladino R., Carlucci P., Danti M.C., Crestini C., Mincione E. Tetrahedron. 56:2000;10031-10037 (i) Bernini R., Mincione E., Cortese M., Aliotta G., Saladino R. Tetrahedron Lett. 42:2001;5401-5404 (j) Iskra J., Bonnet-Delpon D., Bégné J.P. Tetrahedron Lett. 43:2002;1001-1003 (k) Zhu Z., Espenson J.H. J. Org. Chem. 60:1995;7728.
50. See, for example, (b) Herrmann W.A., Fischer R.W., Marz D.W. Angew. Chem, Int. Ed. Engl. 30:1991;1638 (c) Al-Ajlouni A.M., Espenson J.H. J. Org. Chem. 61:1996;3969-3976 (d) Adam W., Mitchell C.M. Angew. Chem., Int. Ed. Engl. 35:1996;533-535 (e) Copéret C., Adolfsson H., Sharpless K.B. J. Chem. Soc., Chem. Commun. 1997;1915 (f) Herrmann W.A., Kratzer R.M., Ding H., Glas H., Thiel W.R. J. Organomet. Chem. 555:1998;293 (g) Adam W., Mitchell C.M., Saha-Moller C.R., Weichold O. J. Am. Chem. Soc. 121:1999;2097-2103 (h) Saladino R., Carlucci P., Danti M.C., Crestini C., Mincione E. Tetrahedron. 56:2000;10031-10037 (i) Bernini R., Mincione E., Cortese M., Aliotta G., Saladino R. Tetrahedron Lett. 42:2001;5401-5404 (j) Iskra J., Bonnet-Delpon D., Bégné J.P. Tetrahedron Lett. 43:2002;1001-1003 (k) Zhu Z., Espenson J.H. J. Org. Chem. 60:1995;7728.
51. See, for example, (b) Herrmann W.A., Fischer R.W., Marz D.W. Angew. Chem, Int. Ed. Engl. 30:1991;1638 (c) Al-Ajlouni A.M., Espenson J.H. J. Org. Chem. 61:1996;3969-3976 (d) Adam W., Mitchell C.M. Angew. Chem., Int. Ed. Engl. 35:1996;533-535 (e) Copéret C., Adolfsson H., Sharpless K.B. J. Chem. Soc., Chem. Commun. 1997;1915 (f) Herrmann W.A., Kratzer R.M., Ding H., Glas H., Thiel W.R. J. Organomet. Chem. 555:1998;293 (g) Adam W., Mitchell C.M., Saha-Moller C.R., Weichold O. J. Am. Chem. Soc. 121:1999;2097-2103 (h) Saladino R., Carlucci P., Danti M.C., Crestini C., Mincione E. Tetrahedron. 56:2000;10031-10037 (i) Bernini R., Mincione E., Cortese M., Aliotta G., Saladino R. Tetrahedron Lett. 42:2001;5401-5404 (j) Iskra J., Bonnet-Delpon D., Bégné J.P. Tetrahedron Lett. 43:2002;1001-1003 (k) Zhu Z., Espenson J.H. J. Org. Chem. 60:1995;7728.
52. See, for example, (b) Herrmann W.A., Fischer R.W., Marz D.W. Angew. Chem, Int. Ed. Engl. 30:1991;1638 (c) Al-Ajlouni A.M., Espenson J.H. J. Org. Chem. 61:1996;3969-3976 (d) Adam W., Mitchell C.M. Angew. Chem., Int. Ed. Engl. 35:1996;533-535 (e) Copéret C., Adolfsson H., Sharpless K.B. J. Chem. Soc., Chem. Commun. 1997;1915 (f) Herrmann W.A., Kratzer R.M., Ding H., Glas H., Thiel W.R. J. Organomet. Chem. 555:1998;293 (g) Adam W., Mitchell C.M., Saha-Moller C.R., Weichold O. J. Am. Chem. Soc. 121:1999;2097-2103 (h) Saladino R., Carlucci P., Danti M.C., Crestini C., Mincione E. Tetrahedron. 56:2000;10031-10037 (i) Bernini R., Mincione E., Cortese M., Aliotta G., Saladino R. Tetrahedron Lett. 42:2001;5401-5404 (j) Iskra J., Bonnet-Delpon D., Bégné J.P. Tetrahedron Lett. 43:2002;1001-1003 (k) Zhu Z., Espenson J.H. J. Org. Chem. 60:1995;7728.
53. Adam W., Hermann W.A., Saha-Moller C.R., Shimizu M. J. Mol. Catal. A. 97:1995;15-20.
54. (a) Adam W., Shimizu M. Synthesis. 1994;560-562.
55. (b) Adam W., Ganeshpure P.A. Synthesis. 1993;280-282.
56. Adam W., Herrmann W.A., Lin J., Saha- Moller C.R. J. Org. Chem. 59:1994;8281.
57. Saladino R., Neri V., Mincione E., Marini S., Coletta M., Fiorucci C., Filippone P. J. Chem. Soc., Perkin Trans. 1. 2000;581-586.
58. Saladino R., Neri V., Pelliccia A.R., Caminiti R., Sadun C. J. Org. Chem. 67:2002;1323-1332.
59. Hermann, W. A.; Fritz-Meyer-Weg, D. M.; Wagner, M.; Kuchler, J. G.; Weichselbaumer, G.; Fischer, R. U.S. Patent 5,155,247 Oct. 13, 1992.
60. Wang T.J., Lì D.C., Bai J.H., Huang M.Y., Jiang Y.Y. J. Macromol. Sci., Pure Appl. Chem. A35:1998;531-538.
61. Adam W., Saha-Moller C.R., Weichold O. J. Org. Chem. 65:2000;2897-2899.
62. Schudel P., Mayer H., Isler O. Sebrell W.H., Harris R.S., The Vitamins. Vol. 5:1994;231 Academic, New York.
63. Shimuzu M., Orita H., Hayakawa T., Watanabe Y., Takehira K. Bull. Chem. Soc. Jpn. 63:1990;1835-1837.
64. Resende N.S., Equino N., Schmal M., Cardoso J.N. J. High Resolut. Chromatogr. 10:1987;576.
65. Tyman J.H. Synthetic and Natural Phenols. 1996;Elsevier, Amsterdam. p 465.
66. Cashew Nut-shell Liquid Patents; The Cashew Export Import Promotion Council, Ernakulam-6, India, 1964, Vols. I and II; See also: www.bolacashew.com.
67. Balint A.V., Dawson J.H., Dawson C.R. Anal. Biochem. 66:1975;340.
68. Amorati R., Pedulli G.F., Valgimigli L., Attanasi O.A., Filippone P., Fiorucci C., Saladino R. J. Chem. Soc., Perkin Trans. 2. 2001;2142-2146.
69. Schuchardt V., Mandelli D., Shulpin G.B. Tetrahedron Lett. 37:1996;6487.
70. Ruokolainen J., Torkkeli M., Serimaa R., Komanschek E., ten Brinke G., Ikkala O. Macromolecole. 30:1997;2002-2007.
71. (a) Limiroli R., Consonni R., Ranalli A., Bianchi G., Zetta L. J. Agric. Food. Chem. 44:1996;2040-2048.
72. (b) Brenes M., Garcìa A., Garcìa P., Rios J.J., Garrido A. J. Agric. Food. Chem. 47:1999;3535-3540.
73. Ochiai E. Aromatic Amine Oxides. 1967;Elsevier, Amsterdam.
74. Resende N.S., Equino Neto F.R., Schmal M., Cardoso J.N. J. High Resolut. Chromatogr. 10:1987;576.
75. Attanasi O.A., Filippone P., Balducci S. Gazz. Chim. Ital. 121:1991;487.
76. From Beilstein; Org. Chem., 7, 645.
77. From Beilstein; Org. Chem., 7, 657.
78. Togo H., Nabana T., Yamaguchi K. J. Org. Chem. 65:2000;8391-8394.